6-(2-Hydroxy-4-phenylbut-3-en-1-yl)-5,6-dihydro-2H-pyran-2-one

Details

• Internal ID: a4e56ea2-ceb1-4c66-b2de-bcf700b508cf
• Taxonomy: Phenylpropanoids and polyketides > Cinnamyl alcohols
• IUPAC Name: 2-(2-hydroxy-4-phenylbut-3-enyl)-2,3-dihydropyran-6-one
• SMILES (Canonical): C1C=CC(=O)OC1CC(C=CC2=CC=CC=C2)O
• SMILES (Isomeric): C1C=CC(=O)OC1CC(C=CC2=CC=CC=C2)O
• InChI: InChI=1S/C15H16O3/c16-13(10-9-12-5-2-1-3-6-12)11-14-7-4-8-15(17)18-14/h1-6,8-10,13-14,16H,7,11H2
• InChI Key: VKRJUPIDWSWXJZ-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₃
• Molecular Weight: 244.28 g/mol
• Exact Mass: 244.109944368 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.32
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• DTXSID90759116
• 6-(2-Hydroxy-4-phenylbut-3-en-1-yl)-5,6-dihydro-2H-pyran-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9751	97.51%
Caco-2	+	0.8191	81.91%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6854	68.54%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9118	91.18%
OATP1B3 inhibitior	+	0.9717	97.17%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.7496	74.96%
P-glycoprotein inhibitior	-	0.9098	90.98%
P-glycoprotein substrate	-	0.8872	88.72%
CYP3A4 substrate	-	0.5730	57.30%
CYP2C9 substrate	-	0.8075	80.75%
CYP2D6 substrate	-	0.8532	85.32%
CYP3A4 inhibition	-	0.8030	80.30%
CYP2C9 inhibition	-	0.9102	91.02%
CYP2C19 inhibition	-	0.5590	55.90%
CYP2D6 inhibition	-	0.9156	91.56%
CYP1A2 inhibition	-	0.9154	91.54%
CYP2C8 inhibition	-	0.7642	76.42%
CYP inhibitory promiscuity	-	0.8196	81.96%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8341	83.41%
Carcinogenicity (trinary)	Non-required	0.5391	53.91%
Eye corrosion	-	0.9296	92.96%
Eye irritation	+	0.7125	71.25%
Skin irritation	+	0.6779	67.79%
Skin corrosion	-	0.8598	85.98%
Ames mutagenesis	-	0.7170	71.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7082	70.82%
Micronuclear	-	0.5338	53.38%
Hepatotoxicity	+	0.5855	58.55%
skin sensitisation	-	0.5976	59.76%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.8071	80.71%
Acute Oral Toxicity (c)	III	0.5117	51.17%
Estrogen receptor binding	+	0.7555	75.55%
Androgen receptor binding	-	0.5618	56.18%
Thyroid receptor binding	-	0.8073	80.73%
Glucocorticoid receptor binding	-	0.5573	55.73%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	-	0.6595	65.95%
Honey bee toxicity	-	0.9119	91.19%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	-	0.4489	44.89%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.36%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.14%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.52%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.03%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.77%	86.33%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.17%	93.99%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.77%	93.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.30%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.57%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	80.48%	94.73%

Plants that contains it

• Cryptocarya liebertiana
• Cryptocarya mandioccana
• Cryptocarya moschata
• Cryptocarya wyliei

Cross-Links

• PubChem: 71330408
• LOTUS: LTS0003315
• wikiData: Q82712970